Abstract: The subject of this research is a set of legal norms that regulate relations in the sphere of challenging of transactions of the debtor, as well as the law enforcement practice. The object of this research is the social relations that develop in the context of challenging of transactions of the debtor in bankruptcy case. The article discusses the problems faced by the arbitration and financial executives at the stage of claim preparation for challenging of transactions of the debtor, i.e. formation of evidence, as well as at the stage of execution of the corresponding court ruling. The purpose goal of this article lies in articulation of the problem, substantiation of the need for legislative regulation, and formulation of recommendation for the improvement of current legislation on the subject matter. The scientific novelty consists in addressed the issues that have not previously become the subject of separate research; as well as in the author’s conclusions and recommendations aimed at the improvement of the Federal Law No. 127-FZ of. October 26, 2002 “On Insolvency (Bankruptcy)” and other normative legal acts regulating this field. The acquired results can also be used in the Russian legal science for further elaboration on the issues related to the effectiveness of the mechanism for challenging of transactions of the debtor, and as well as improvement of the current legislation of the Russian Federation and law enforcement practice that regulate this field.